SG183699A1 - Heteroaryl amide analogues - Google Patents

Info

Publication number

SG183699A1

SG183699A1 SG2012058533A SG2012058533A SG183699A1 SG 183699 A1 SG183699 A1 SG 183699A1 SG 2012058533 A SG2012058533 A SG 2012058533A SG 2012058533 A SG2012058533 A SG 2012058533A SG 183699 A1 SG183699 A1 SG 183699A1

Authority

SG

Singapore

Prior art keywords

pyrimidin

indole

carboxamide

compound

hydrate

Prior art date

2007-08-10

Links

• Espacenet
• Global Dossier
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• -1 Heteroaryl amide Chemical class 0.000 title claims abstract description 126
• 150000001875 compounds Chemical class 0.000 claims abstract description 267
• 208000002193 Pain Diseases 0.000 claims abstract description 87
• 230000036407 pain Effects 0.000 claims abstract description 81
• 238000000034 method Methods 0.000 claims abstract description 58
• 239000000556 agonist Substances 0.000 claims abstract description 28
• 238000011282 treatment Methods 0.000 claims abstract description 25
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 23
• 206010061218 Inflammation Diseases 0.000 claims abstract description 18
• 230000004054 inflammatory process Effects 0.000 claims abstract description 18
• 208000024172 Cardiovascular disease Diseases 0.000 claims abstract description 8
• 208000015122 neurodegenerative disease Diseases 0.000 claims abstract description 8
• 208000022873 Ocular disease Diseases 0.000 claims abstract description 7
• 208000012902 Nervous system disease Diseases 0.000 claims abstract description 5
• 208000026278 immune system disease Diseases 0.000 claims abstract description 5
• 230000000926 neurological effect Effects 0.000 claims abstract 4
• 102000005962 receptors Human genes 0.000 claims description 103
• 108020003175 receptors Proteins 0.000 claims description 103
• 239000000203 mixture Substances 0.000 claims description 92
• 150000003839 salts Chemical class 0.000 claims description 81
• 230000000694 effects Effects 0.000 claims description 67
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 66
• LSGKMZLPZFPAIN-UHFFFAOYSA-N 1h-indole-3-carboxamide Chemical compound C1=CC=C2C(C(=O)N)=CNC2=C1 LSGKMZLPZFPAIN-UHFFFAOYSA-N 0.000 claims description 54
• 238000003556 assay Methods 0.000 claims description 50
• 150000003857 carboxamides Chemical class 0.000 claims description 48
• 229910052736 halogen Inorganic materials 0.000 claims description 47
• 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 46
• 150000002367 halogens Chemical class 0.000 claims description 46
• 125000001424 substituent group Chemical group 0.000 claims description 42
• 125000000217 alkyl group Chemical group 0.000 claims description 36
• 210000004027 cell Anatomy 0.000 claims description 36
• 125000001072 heteroaryl group Chemical group 0.000 claims description 36
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 35
• 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 34
• 229910052799 carbon Inorganic materials 0.000 claims description 32
• 125000000623 heterocyclic group Chemical group 0.000 claims description 32
• 229910052739 hydrogen Inorganic materials 0.000 claims description 32
• 125000004429 atom Chemical group 0.000 claims description 31
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 29
• 239000001257 hydrogen Substances 0.000 claims description 28
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 26
• 208000004296 neuralgia Diseases 0.000 claims description 25
• 239000003814 drug Substances 0.000 claims description 21
• 229910052702 rhenium Inorganic materials 0.000 claims description 21
• 125000003118 aryl group Chemical group 0.000 claims description 20
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 20
• 229910052757 nitrogen Inorganic materials 0.000 claims description 20
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 17
• 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 16
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
• 150000001721 carbon Chemical group 0.000 claims description 15
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 15
• 125000004043 oxo group Chemical group O=* 0.000 claims description 15
• 125000002947 alkylene group Chemical group 0.000 claims description 14
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 14
• 206010016654 Fibrosis Diseases 0.000 claims description 12
• 239000002253 acid Substances 0.000 claims description 12
• 208000006673 asthma Diseases 0.000 claims description 12
• 238000000338 in vitro Methods 0.000 claims description 11
• 208000021722 neuropathic pain Diseases 0.000 claims description 11
• 229910052760 oxygen Inorganic materials 0.000 claims description 11
• AINBWHVBVYQQAZ-UHFFFAOYSA-N 4-chloro-1-pyrimidin-2-ylindole-3-carboxylic acid Chemical compound C12=CC=CC(Cl)=C2C(C(=O)O)=CN1C1=NC=CC=N1 AINBWHVBVYQQAZ-UHFFFAOYSA-N 0.000 claims description 10
• 206010029240 Neuritis Diseases 0.000 claims description 10
• 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 10
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 10
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 10
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 10
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 10
• 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 9
• 206010039073 rheumatoid arthritis Diseases 0.000 claims description 9
• 208000011580 syndromic disease Diseases 0.000 claims description 9
• 230000001154 acute effect Effects 0.000 claims description 8
• 125000003545 alkoxy group Chemical group 0.000 claims description 8
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• 239000000126 substance Substances 0.000 claims description 7
• 238000006467 substitution reaction Methods 0.000 claims description 7
• 208000023275 Autoimmune disease Diseases 0.000 claims description 6
• WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 6
• 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 6
• 150000001412 amines Chemical class 0.000 claims description 6
• 125000002837 carbocyclic group Chemical group 0.000 claims description 6
• 210000003169 central nervous system Anatomy 0.000 claims description 6
• 239000006071 cream Substances 0.000 claims description 6
• 239000001301 oxygen Substances 0.000 claims description 6
• 125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 claims description 6
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
• 208000030886 Traumatic Brain injury Diseases 0.000 claims description 5
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 5
• 229910002091 carbon monoxide Inorganic materials 0.000 claims description 5
• 230000034994 death Effects 0.000 claims description 5
• 239000007788 liquid Substances 0.000 claims description 5
• 206010025135 lupus erythematosus Diseases 0.000 claims description 5
• 239000000825 pharmaceutical preparation Substances 0.000 claims description 5
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• 201000005569 Gout Diseases 0.000 claims description 4
• 206010039710 Scleroderma Diseases 0.000 claims description 4
• ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical compound C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 claims description 4
• 230000008484 agonism Effects 0.000 claims description 4
• 125000000278 alkyl amino alkyl group Chemical group 0.000 claims description 4
• 125000000304 alkynyl group Chemical group 0.000 claims description 4
• 206010003246 arthritis Diseases 0.000 claims description 4
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
• CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 claims description 4
• 230000007882 cirrhosis Effects 0.000 claims description 4
• 208000019425 cirrhosis of liver Diseases 0.000 claims description 4
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 4
• 230000002401 inhibitory effect Effects 0.000 claims description 4
• 208000002551 irritable bowel syndrome Diseases 0.000 claims description 4
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
• 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 4
• 125000001544 thienyl group Chemical group 0.000 claims description 4
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
• 229910052721 tungsten Inorganic materials 0.000 claims description 4
• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 3
• 239000005711 Benzoic acid Substances 0.000 claims description 3
• 206010019233 Headaches Diseases 0.000 claims description 3
• 206010028391 Musculoskeletal Pain Diseases 0.000 claims description 3
• 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 3
• 239000000443 aerosol Substances 0.000 claims description 3
• 235000010233 benzoic acid Nutrition 0.000 claims description 3
• 239000002775 capsule Substances 0.000 claims description 3
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 3
• 125000004663 dialkyl amino group Chemical group 0.000 claims description 3
• 231100000869 headache Toxicity 0.000 claims description 3
• 125000004475 heteroaralkyl group Chemical group 0.000 claims description 3
• ZVTQYRVARPYRRE-UHFFFAOYSA-N oxadiazol-4-one Chemical compound O=C1CON=N1 ZVTQYRVARPYRRE-UHFFFAOYSA-N 0.000 claims description 3
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
• 208000005069 pulmonary fibrosis Diseases 0.000 claims description 3
• 125000004076 pyridyl group Chemical group 0.000 claims description 3
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 3
• 230000008653 root damage Effects 0.000 claims description 3
• 238000001356 surgical procedure Methods 0.000 claims description 3
• 239000006188 syrup Substances 0.000 claims description 3
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• 150000003536 tetrazoles Chemical class 0.000 claims description 3
• 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 2
• 206010002383 Angina Pectoris Diseases 0.000 claims description 2
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• 206010014020 Ear pain Diseases 0.000 claims description 2
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• 208000033830 Hot Flashes Diseases 0.000 claims description 2
• 206010060800 Hot flush Diseases 0.000 claims description 2
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• 206010042496 Sunburn Diseases 0.000 claims description 2
• 125000003342 alkenyl group Chemical group 0.000 claims description 2
• 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
• 125000004103 aminoalkyl group Chemical group 0.000 claims description 2
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• 208000014439 complex regional pain syndrome type 2 Diseases 0.000 claims description 2
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• 125000003106 haloaryl group Chemical group 0.000 claims description 2
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• 238000004519 manufacturing process Methods 0.000 claims description 2
• 125000002757 morpholinyl group Chemical group 0.000 claims description 2
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• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 2
• XUSXTHMTOSFZII-UHFFFAOYSA-N 1-(aminomethyl)cyclohexan-1-ol Chemical compound NCC1(O)CCCCC1 XUSXTHMTOSFZII-UHFFFAOYSA-N 0.000 claims 1
• RHRYWWVGUVEZRJ-UHFFFAOYSA-N 2,3-diphenylpropylamine Chemical compound C=1C=CC=CC=1C(CN)CC1=CC=CC=C1 RHRYWWVGUVEZRJ-UHFFFAOYSA-N 0.000 claims 1
• ZGOBGVMDCXQRKY-UHFFFAOYSA-N 2-(4-chlorophenyl)-4-methylpentan-1-amine Chemical compound CC(C)CC(CN)C1=CC=C(Cl)C=C1 ZGOBGVMDCXQRKY-UHFFFAOYSA-N 0.000 claims 1
• SQMNYSQPHYHTSO-UHFFFAOYSA-N 2-phenylpentan-1-amine Chemical compound CCCC(CN)C1=CC=CC=C1 SQMNYSQPHYHTSO-UHFFFAOYSA-N 0.000 claims 1
• LMGLILPGKZPDAX-UHFFFAOYSA-N 3-cyclopentyl-2-phenylpropan-1-amine Chemical compound C=1C=CC=CC=1C(CN)CC1CCCC1 LMGLILPGKZPDAX-UHFFFAOYSA-N 0.000 claims 1
• HJMCIHLESAJJQL-UHFFFAOYSA-N 3-phenylbutan-1-amine Chemical compound NCCC(C)C1=CC=CC=C1 HJMCIHLESAJJQL-UHFFFAOYSA-N 0.000 claims 1
• WSPSZBVPJYACII-UHFFFAOYSA-N 4-chloro-n-(2-cyclohexyl-2-phenylethyl)-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1=2C(Cl)=CC=CC=2N(C=2N=CC=CN=2)C=C1C(=O)NCC(C=1C=CC=CC=1)C1CCCCC1 WSPSZBVPJYACII-UHFFFAOYSA-N 0.000 claims 1
• NQIVGAXWGWVAGP-UHFFFAOYSA-N 4-chloro-n-(3-methylbutyl)-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C12=CC=CC(Cl)=C2C(C(=O)NCCC(C)C)=CN1C1=NC=CC=N1 NQIVGAXWGWVAGP-UHFFFAOYSA-N 0.000 claims 1
• ZHQIUAHDKPUOKT-UHFFFAOYSA-N 4-chloro-n-[2-(4-chlorophenyl)-2-morpholin-4-ylethyl]-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1=CC(Cl)=CC=C1C(N1CCOCC1)CNC(=O)C(C1=C(Cl)C=CC=C11)=CN1C1=NC=CC=N1 ZHQIUAHDKPUOKT-UHFFFAOYSA-N 0.000 claims 1
• VZMLUTLVCOGUEI-UHFFFAOYSA-N 4-chloro-n-[2-(4-chlorophenyl)-2-piperazin-1-ylethyl]-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1=CC(Cl)=CC=C1C(N1CCNCC1)CNC(=O)C(C1=C(Cl)C=CC=C11)=CN1C1=NC=CC=N1 VZMLUTLVCOGUEI-UHFFFAOYSA-N 0.000 claims 1
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• JLLYLQLDYORLBB-UHFFFAOYSA-N 5-bromo-n-methylthiophene-2-sulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(Br)S1 JLLYLQLDYORLBB-UHFFFAOYSA-N 0.000 claims 1
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• ROSDSFDQCJNGOL-UHFFFAOYSA-N protonated dimethyl amine Natural products CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims 1
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